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Jack and Bill - Chapter 1
"I'm just saying," Bill told Jack, "that I wonder what it feels like. I mean, gay guys do it all the time right? So... well, there must be something, like, good about it."Jack flopped down on the grass near the pond that he and Bill had just gotten out of. The two young men were hiking and sweating on a hot day when they happened upon the small pond surrounded by trees with a small grassy area on one side. Neither had a swim suit, so they'd stripped down and ran into the clear, cool water. Bill sat next to Jack on the grass. They were still naked, letting the sun dry them off.
"I guess so," said Jack, "Seems, like, dirty, but yeah, why else would you take it up the ass unless it felt good somehow. Why? You wanna find out? Get fucked in the butt?"
"Fuck no!" Bill said, sounding pissed, but then more quietly, "No, I don't want some guy's big dick up my ass, I'm just saying... I heard sometimes a girl will slide her finger in there while she's giving a guy head."
"Oh. Yeah. I've heard of that. Never happened to me, but I guess..."
"Could be cool, right? Not sure I could ever ask a girl to do that really, but I think I might like it, y'know?"
"Well, want me to, like, do it? To you?" Jack surprised them both by asking.
"You mean you'd...?"
"I'm mot gonna suck your dick, dude! But if you wanna know what it feels like to have something in your ass, I'll stick a finger in there for ya. It's not a big deal."
"Um, yeah. Okay. Should I... How should I be? Like, laying on my stomach, or...?"
"Well, how about on your hands and knees? That way I can see what I'm working with."
Bill got into position in front of Jack. He had his legs spread enough so that Jack could see between his asscheeks to the puckered hole there. It looked clean and pink and the hairs around it were still damp from the swim. Jack liked the look of his buddy's asshole and the way he was showing it to him made him feel a little funny. Better get this over with quick, he thought, I don't want Bill to see me getting a boner from looking at his ass.
Bill felt funny too, naked and on his hands and knees, ass spread in front of his friend. He could feel the warm air on his anus and he wanted this, had for a while, even though he had to admit to himself that he didn't know exactly what 'this' was.
"Go ahead, man," He said over hi shoulder, "I'm ready."
Jack knelt down behind Bill. He put one hand on his friend's ass and brought the index finger of the other to within an inch of his asshole. He paused for a second, then went ahead and touched him there. It felt wrinkly and really tight, and when Jack tried to push the tip of his finger in, it went nowhere.
"Ow," said Bill.
"Sorry, but it's way too tight bro. I don't know how a guy could ever take anything in there, it's like... closed."
"They use lube I guess. You gotta get it slippery somehow. Spit maybe?"
"Um, okay," Jack said and leaning over, brought his mouth close to Bill's ass. He worked up some spit and let it fall, missing the hole but not the crack higher up. He watched as it dripped down and when it got to his buddy's pucker, he tried agin with his finger. It still felt very tight, but when Jack applied a little pressure, his finger popped right into Bill's anus.
"Oh!" Bill said.
"Is it...? Is that okay? Should I take it out?"
"No, no, I just... It's okay, just wait a second."
Jack waited, feeling increasingly weird, kneeling behind his friend with his finger halfway up his ass. Bill started to move slightly, causing Jack's finger to go a little deeper, then pull out a little. It felt crazy and Jack wasn't freaking out, but almost, as he watched his buddy push back and take more inside him. Also, Jack's cock was starting to thicken a little. He pulled his finger out of Bill's butt, turned quickly to hide his arousal, and ran into the water.
Bill yelped from the abrupt withdrawal. Oddly, Jack's finger being pulled out caused him more discomfort than when he'd pushed it in. He knelt there for a few seconds - it had started to feel... well, kind of good. That was weird, Bill thought.
Jack turned in the water in time to see Bill get up and run in, the splashing water not enough to hide the young man's waving erection.